
1002 OAKDALE STREET, WINDERMERE, FL, 34786
Pending110 days on marketListed Apr 14, 2026MLS #TB8495717
About this home
1002 OAKDALE STREET
Set on a prominent corner lot in one of Windermere’s most sought-after enclaves, this thoughtfully updated residence blends timeless character with modern upgrades, enormous walk out bottom level, massive multiple garages and a lifestyle that is uniquely local to this area. Relax on the expansive front porch and take in the surroundings as neighbors and nature pass by. Recent improvements include a new roof, a fully renovated kitchen, a designer-inspired primary bath, fresh interior and exterior paint, and newer engineered wood flooring, creating a cohesive, move-in ready home with a refined, modern feel. The layout offers expansive living spaces filled with natural light, designed for both everyday comfort and effortless entertaining. The primary suite serves as a true retreat, highlighted by a beautifully reimagined bath featuring a freestanding soaking tub, custom tile work, and a double vanity. Additional living areas and a spacious lower level provide flexibility for a media room, home office, fitness space, or guest accommodations. A rare offering in this location, the property features an impressive 3 bay, 30' long garage on one end and an additional garage bay on the opposite end of the home., ideal for collectors, storage, or workshop needs. Positioned along historic Windermere’s signature tree-lined dirt roads, the setting offers a level of charm and privacy that is increasingly hard to find. Residents enjoy exclusive access to city tennis courts and a private dock with entry to the interconnected lake chain that surrounds this community, delivering a true lake lifestyle just moments from home. Seller is open to negotiating a closing cost credit, providing added flexibility and value for buyers for closing costs or rate buy down. A compelling combination of location, scale, and thoughtful updates—this is Windermere living at its best.
Facts & features
The home at a glance
4
Bedrooms
3
Bathrooms
3,516
Sqft
0.29 ac
Lot size
4
Garage
1973
Year built
One
Levels
$270
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$6,376 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:

Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$6,376/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Where it sits
Inside Windermere
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Windermere. See the full Windermere guide →
WINDERMERE 34786 — neighborhood snapshot
Population
43,700
Median age
37.9
Median income
$131,409
Median home value
$621,300
Avg household
2.9
Households w/ children
6,277
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Windermere market
$839K → $1.0M
Windermere median sold, yr/yr
96.4%
Sale-to-list ratio (12 mo)
Median sold price, Windermere, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 19% above the WINDERMERE 34786 median. See the full Windermere market guide →
Paper trail
This home's history
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 1002 OAKDALE STREET — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1002 OAKDALE STREET — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
1002 OAKDALE STREET FAQs
What would the monthly payment be for 1002 OAKDALE STREET?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $6,376/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 1002 OAKDALE STREET?+
The most recent tax bill on record (2025) was $8,799. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
How does the price compare to other homes in Windermere?+
At $950,000, this home is listed about 14% below the Windermere median of $1,099,500. The market section on this page shows how the area is trending.
Which schools are assigned to 1002 OAKDALE STREET?+
Windermere Elementary (elementary), Olympia High (high), Gotha Middle (middle) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Four things that matter here
01Positioned at the premium end
$950,000 runs 19% above the WINDERMERE 34786 median.
02Time on market is leverage
110 days on market against a Windermere median of 32 — sellers in this position are usually ready to negotiate.
03Strong assigned schools
Windermere Elementary, Olympia High, Gotha Middle — Windermere Elementary rates 5 of 5. Always verify assignments with the district.
04The price has already moved
Listed at $975,000, now $950,000 — a $25K cut. The full history is in the market section below.
Listing courtesy of KELLER WILLIAMS SUBURBAN TAMPA · Frank Smith. MLS #TB8495717.
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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